1-(METHYLAMINO)ADAMANTANE Chemical Properties

Boiling point:

226.8±8.0℃ (760 Torr)

Density 

1.00±0.1 g/cm3 (20 ºC 760 Torr)

Flash point:

84.0±15.8℃

pka

11.32±0.20(Predicted)

form 

lumps

BRN 

2348926

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

AU4375400

Toxicity

mouse,LD50,intraperitoneal,175mg/kg (175mg/kg),Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 14(3), Pg. 59, 1980.

1-(METHYLAMINO)ADAMANTANE Usage And Synthesis

Synthesis

1) In a glove box, 0.25 mmol of amantadine, 6 equivalents (1.5 mmol) of diphenylsilane, 10 mol% (based on amantadine) of cesium carbonate, and 1.6 mL of acetonitrile solvent were added to 50 mL of N2-protected Schlenk tubes.2) The N2 in the Schlenk tubes was replaced by CO2 in the double-rowed tubes by a refrigeration vacuum operation to regulate the CO2 pressure to 1 bar.3) The reaction was carried out in acetonitrile solvent at 80 °C for 72 h using cesium carbonate as catalyst, CO2 as C1 source, and diphenylsilane as reductant.4) At the end of the reaction, 0.2 mmol of ferrocene was added to the Schlenk tubes as an internal standard.5) The NMR spectra of the resulting products were analyzed by Bruker NMR analysis, which showed a similarity to the NMR spectra of the products reported in the literature (P. Besenius, P. A. G. Cormack, R. F. Ludlow, S. Otto, D. C. Sherrington, Chem. Commun. 2008) for pure N-methyl-1-adamantanamine, and the product yield was >95% under the conditions of this experiment.

References

[1] Patent: CN105753715, 2016, A. Location in patent: Paragraph 0029; 0030; 0031; 0032; 0033; 0034; 0035
[2] ACS Catalysis, 2016, vol. 6, # 11, p. 7876 - 7881

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